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I was actually planning for a workation there, and I found that this is actually a great time to visit Mcleodganj. If you are touring there for just a few days, you can avail travel packages for triund trek. I would also recommend the following places...
1. Lam dal lake
2. Ghera Waterfalls
3. Laka Glacier
4. Shepherd's cave
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Yes, unless you have health issues, mid october is quite a beautiful time to visit Dharamshala and Macleodganj.
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Oct would be good to visit McLeodganj. Visit the Bhagsu Falls and walk upto Shiva cafe. It's a quaint little place up hill. There are innumerable cafe's. You can enjoy sumptuous meal in there. If you want you can trek to Triund also.
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